In a preview clip of Oprah's Next Chapter, Winfrey asks questions like "Do you think you are addicted to chaos?" and "What's going to be different this time?"
The highly anticipated show is slated to air in the US on August 18, reported Us magazine.
Lohan, 27, was released from rehab on July 30 after completing a court-mandated 90-day stint. She has spent 293 days in rehab since her first stint in 2007.
Winfrey asks Lohan questions like "What does it feel like to be -- both an adjective and a verb -- for a child actor gone wrong?"
"And we'll see. I'm anxious to see whether or not this young woman, who is a really, really fine actress, will be able to allow us into her life and let us see the trajectory of trying to put the pieces back together," Winfrey told Al Roker on the Today Show.
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